N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents

Abstract

This invention relates to N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole compounds of formula I <CHEM> It also relates to the use of said compounds as insecticidal and acaricidal agents and to a method of protecting plants from attack by insects and acarina by application of an N-alkanoylaminomethyl or N-aroylaminomethyl pyrrole to said plants or to the locus in which they are growing.

I claim: 
     
       1. A compound having the structural formula ##STR11## wherein W is halogen, CN or NO 2  ; X is halogen or phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups;   Y is halogen, CF 3  or phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups;   Z is halogen or CF 3  ;   R 1  is hydrogen or C 1  -C 4  alkyl; and   R is C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups,   2- or 3-thienyl or   2- or 3-furyl; provided that when W is halogen, then X is phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups and Y and Z are CF 3 .       
     
     
       2. The compound according to claim 1 wherein W is CN or NO 2  ;   X is phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups;   Y is halogen or CF 3  ;   Z is halogen or CF 3  ;   R 1  is hydrogen; and   R is C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups,   2- or 3-thienyl or   2- or 3-furyl.     
     
     
       3. The compound according to claim 2 wherein X is phenyl optionally substituted with one or two halogen or CF 3  groups;   Y is Cl, Br or CF 3  ;   Z is Cl, Br or CF 3  ; and   R is C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, phenyl optionally substituted with one or two halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups, or   2- or 3-thienyl.     
     
     
       4. The compound according to claim 3 N-{[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl}acetamide. 
     
     
       5. The compound according to claim 3 N-{[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl}benzamide. 
     
     
       6. The compound according to claim 3 N-{[3-bromo-5-(p-chlorophenyl)-4-cyano-2-(trifluoromethyl)pyrrol-1-yl]methyl}-2-thiophenecarboxamide. 
     
     
       7. The compound according to claim 3 N-{[2,3-dichloro-4-cyano-5-(3,4-dichlorophenyl)pyrrol-1-yl]methyl}acetamide. 
     
     
       8. A composition for controlling insects and acarina comprising an agronomically acceptable carrier and an insecticidally or acaricidally effective amount of a compound having the structural formula ##STR12## wherein W is halogen, CN or NO 2  ; X is halogen or phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups;   Y is halogen, CF 3  or phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups;   Z is halogen or CF 3  ;   R 1  is hydrogen or C 1  -C 4  alkyl; and   R is C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkyl, C 1  -C 4  alkoxy or CF 3  groups,   2- or 3-thienyl or   2- or 3-furyl; provided that when W is halogen, then X is phenyl optionally substituted with one or two halogen, CN, NO 2 , C 1  -C 4  alkoxy or CF 3  groups and Y and Z are CF 3 .